KR20200027545A - 지방산 유도체 및 이의 용도 - Google Patents
지방산 유도체 및 이의 용도 Download PDFInfo
- Publication number
- KR20200027545A KR20200027545A KR1020207003568A KR20207003568A KR20200027545A KR 20200027545 A KR20200027545 A KR 20200027545A KR 1020207003568 A KR1020207003568 A KR 1020207003568A KR 20207003568 A KR20207003568 A KR 20207003568A KR 20200027545 A KR20200027545 A KR 20200027545A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- epoxy
- hydroxy
- substituted
- hydrogen
- Prior art date
Links
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 title abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- 208000002193 Pain Diseases 0.000 claims abstract description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 85
- 239000001257 hydrogen Substances 0.000 claims abstract description 85
- 208000003251 Pruritus Diseases 0.000 claims abstract description 83
- 230000007803 itching Effects 0.000 claims abstract description 73
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 45
- 230000004054 inflammatory process Effects 0.000 claims abstract description 32
- 206010061218 Inflammation Diseases 0.000 claims abstract description 31
- 230000001684 chronic effect Effects 0.000 claims abstract description 28
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 25
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 19
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 208000017520 skin disease Diseases 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 12
- 150000003573 thiols Chemical class 0.000 claims abstract description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 11
- 150000004820 halides Chemical class 0.000 claims abstract description 11
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 62
- 201000010099 disease Diseases 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 230000001965 increasing effect Effects 0.000 claims description 41
- 239000004593 Epoxy Substances 0.000 claims description 37
- 201000004681 Psoriasis Diseases 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical class CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 26
- 239000012472 biological sample Substances 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 150000001345 alkine derivatives Chemical class 0.000 claims description 10
- 235000005911 diet Nutrition 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 206010003246 arthritis Diseases 0.000 claims description 9
- 201000008937 atopic dermatitis Diseases 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 230000037213 diet Effects 0.000 claims description 9
- 201000004624 Dermatitis Diseases 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 206010021198 ichthyosis Diseases 0.000 claims description 5
- 206010013786 Dry skin Diseases 0.000 claims description 4
- 230000037336 dry skin Effects 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 108010024636 Glutathione Proteins 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 230000005549 barrier dysfunction Effects 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- 229960003180 glutathione Drugs 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 210000000981 epithelium Anatomy 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- YQMUORJJDBQCOV-UHFFFAOYSA-N $l^{1}-phosphanylmethane Chemical compound [P]C YQMUORJJDBQCOV-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 210000004400 mucous membrane Anatomy 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- -1 carbon Forms alkyne Chemical group 0.000 abstract description 33
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 abstract description 13
- 150000007824 aliphatic compounds Chemical group 0.000 abstract description 4
- 229910021386 carbon form Inorganic materials 0.000 abstract description 3
- 210000003491 skin Anatomy 0.000 description 84
- 239000000194 fatty acid Substances 0.000 description 82
- 235000014113 dietary fatty acids Nutrition 0.000 description 81
- 229930195729 fatty acid Natural products 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 78
- 150000004665 fatty acids Chemical class 0.000 description 77
- 230000036407 pain Effects 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000002253 acid Substances 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
- 150000002632 lipids Chemical class 0.000 description 46
- 239000000203 mixture Substances 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 241000700159 Rattus Species 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 210000001519 tissue Anatomy 0.000 description 33
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 32
- 208000024891 symptom Diseases 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 238000011282 treatment Methods 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- 102000004414 Calcitonin Gene-Related Peptide Human genes 0.000 description 25
- 108090000932 Calcitonin Gene-Related Peptide Proteins 0.000 description 25
- 230000032050 esterification Effects 0.000 description 25
- 238000005886 esterification reaction Methods 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 230000004044 response Effects 0.000 description 24
- 206010019233 Headaches Diseases 0.000 description 23
- 230000000694 effects Effects 0.000 description 22
- 235000013305 food Nutrition 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- 238000002347 injection Methods 0.000 description 22
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 21
- 239000003814 drug Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 206010003210 Arteriosclerosis Diseases 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 231100000869 headache Toxicity 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 229940089161 ginsenoside Drugs 0.000 description 17
- 229930182494 ginsenoside Natural products 0.000 description 17
- 230000009467 reduction Effects 0.000 description 17
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical class CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 16
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 16
- 235000012000 cholesterol Nutrition 0.000 description 16
- 239000000523 sample Substances 0.000 description 16
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 14
- 230000014759 maintenance of location Effects 0.000 description 14
- 210000001044 sensory neuron Anatomy 0.000 description 14
- QOZMNTOLZYSKJT-UHFFFAOYSA-N 16-(oxiren-2-yl)-16-oxohexadecanoic acid Chemical class O=C(C1=CO1)CCCCCCCCCCCCCCC(=O)O QOZMNTOLZYSKJT-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 208000015181 infectious disease Diseases 0.000 description 13
- 230000003902 lesion Effects 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 238000006748 scratching Methods 0.000 description 13
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
- 229930194542 Keto Natural products 0.000 description 12
- 230000006399 behavior Effects 0.000 description 12
- 239000011575 calcium Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 230000002757 inflammatory effect Effects 0.000 description 12
- 210000002381 plasma Anatomy 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 230000002393 scratching effect Effects 0.000 description 12
- 210000003594 spinal ganglia Anatomy 0.000 description 12
- 102000005666 Apolipoprotein A-I Human genes 0.000 description 11
- 108010059886 Apolipoprotein A-I Proteins 0.000 description 11
- 238000003556 assay Methods 0.000 description 11
- 230000004888 barrier function Effects 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 210000002966 serum Anatomy 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 10
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 10
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 10
- 230000014509 gene expression Effects 0.000 description 10
- 235000020778 linoleic acid Nutrition 0.000 description 10
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 10
- 230000001404 mediated effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 9
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 238000012384 transportation and delivery Methods 0.000 description 9
- 241000283984 Rodentia Species 0.000 description 8
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
- 235000017663 capsaicin Nutrition 0.000 description 8
- 229960002504 capsaicin Drugs 0.000 description 8
- 229960002986 dinoprostone Drugs 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- 125000000468 ketone group Chemical group 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000000451 tissue damage Effects 0.000 description 8
- 231100000827 tissue damage Toxicity 0.000 description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- 102100027971 Arachidonate 12-lipoxygenase, 12R-type Human genes 0.000 description 7
- 208000035473 Communicable disease Diseases 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 7
- 206010070834 Sensitisation Diseases 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 230000000975 bioactive effect Effects 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 210000000548 hind-foot Anatomy 0.000 description 7
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 7
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 7
- 230000005070 ripening Effects 0.000 description 7
- 230000008313 sensitization Effects 0.000 description 7
- 206010040882 skin lesion Diseases 0.000 description 7
- 231100000444 skin lesion Toxicity 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000011200 topical administration Methods 0.000 description 7
- 241000282412 Homo Species 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000002158 endotoxin Substances 0.000 description 6
- 230000000763 evoking effect Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- 229920006008 lipopolysaccharide Polymers 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- KPWVFNOPNOTYNJ-UHFFFAOYSA-N octadecyl benzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 KPWVFNOPNOTYNJ-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 230000001185 psoriatic effect Effects 0.000 description 6
- 238000011002 quantification Methods 0.000 description 6
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 6
- 210000003497 sciatic nerve Anatomy 0.000 description 6
- 230000028327 secretion Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 6
- QGIKMVDHNBCWDH-UHFFFAOYSA-N 16-(3-hydroxyoxiren-2-yl)hexadecanoic acid Chemical compound OC1=C(CCCCCCCCCCCCCCCC(=O)O)O1 QGIKMVDHNBCWDH-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 208000003098 Ganglion Cysts Diseases 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 102100027921 Polyunsaturated fatty acid lipoxygenase ALOX15B Human genes 0.000 description 5
- 208000005400 Synovial Cyst Diseases 0.000 description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 238000001574 biopsy Methods 0.000 description 5
- 230000001851 biosynthetic effect Effects 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 230000002354 daily effect Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 230000004770 neurodegeneration Effects 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 230000003040 nociceptive effect Effects 0.000 description 5
- 150000002924 oxiranes Chemical group 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 230000001953 sensory effect Effects 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- IEPGNWMPIFDNSD-HZJYTTRNSA-N 2-linoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(CO)CO IEPGNWMPIFDNSD-HZJYTTRNSA-N 0.000 description 4
- QOQZBXWYKMUHKK-UHFFFAOYSA-N 9,10,13-trihydroxyoctadec-2-enoic acid Chemical compound CCCCCC(O)CCC(O)C(O)CCCCCC=CC(O)=O QOQZBXWYKMUHKK-UHFFFAOYSA-N 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- 208000016192 Demyelinating disease Diseases 0.000 description 4
- 206010012305 Demyelination Diseases 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- 101000578469 Homo sapiens Arachidonate 12-lipoxygenase, 12R-type Proteins 0.000 description 4
- 101000578474 Homo sapiens Polyunsaturated fatty acid lipoxygenase ALOX15B Proteins 0.000 description 4
- 108010063738 Interleukins Proteins 0.000 description 4
- 102000015696 Interleukins Human genes 0.000 description 4
- 102000004882 Lipase Human genes 0.000 description 4
- 108090001060 Lipase Proteins 0.000 description 4
- 239000004367 Lipase Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000012491 analyte Substances 0.000 description 4
- 235000021342 arachidonic acid Nutrition 0.000 description 4
- 229940114079 arachidonic acid Drugs 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000005784 autoimmunity Effects 0.000 description 4
- 230000003542 behavioural effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 201000001981 dermatomyositis Diseases 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 238000007273 lactonization reaction Methods 0.000 description 4
- 235000019421 lipase Nutrition 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 210000003739 neck Anatomy 0.000 description 4
- 210000005036 nerve Anatomy 0.000 description 4
- 230000001537 neural effect Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 150000004685 tetrahydrates Chemical class 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 3
- YJQVLUXUKMSFBT-UHFFFAOYSA-N 8-[3-(3-hydroxyoctyl)oxiran-2-yl]oct-2-enoic acid Chemical compound O1C(CCCCCC=CC(=O)O)C1CCC(CCCCC)O YJQVLUXUKMSFBT-UHFFFAOYSA-N 0.000 description 3
- PSSQXFYUVUASTM-UHFFFAOYSA-N 9-oxo-11-(3-pentyloxiran-2-yl)undec-2-enoic acid Chemical compound CCCCCC1OC1CCC(=O)CCCCCC=CC(O)=O PSSQXFYUVUASTM-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 101710184162 Arachidonate 12-lipoxygenase, 12R-type Proteins 0.000 description 3
- FJMOPOQSKRQWHD-XJQDBPQSSA-N CCCCC\C(O)=C/C\C(O)=C(\O)CCCCCCC(C)(C)C(O)=O Chemical compound CCCCC\C(O)=C/C\C(O)=C(\O)CCCCCCC(C)(C)C(O)=O FJMOPOQSKRQWHD-XJQDBPQSSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 206010016260 Fatty acid deficiency Diseases 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 102100022363 Hydroperoxide isomerase ALOXE3 Human genes 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 206010065390 Inflammatory pain Diseases 0.000 description 3
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
- 238000012313 Kruskal-Wallis test Methods 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- 238000004617 QSAR study Methods 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- 238000010811 Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry Methods 0.000 description 3
- 208000005298 acute pain Diseases 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 201000004983 autoimmune atherosclerosis Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 229960001948 caffeine Drugs 0.000 description 3
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- PRHHYVQTPBEDFE-UHFFFAOYSA-N eicosatrienoic acid Natural products CCCCCC=CCC=CCCCCC=CCCCC(O)=O PRHHYVQTPBEDFE-UHFFFAOYSA-N 0.000 description 3
- 210000002615 epidermis Anatomy 0.000 description 3
- 238000010931 ester hydrolysis Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 210000000609 ganglia Anatomy 0.000 description 3
- 125000005908 glyceryl ester group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000009610 hypersensitivity Effects 0.000 description 3
- 210000000987 immune system Anatomy 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 3
- 210000003622 mature neutrocyte Anatomy 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 230000035807 sensation Effects 0.000 description 3
- 210000000413 sensory ganglia Anatomy 0.000 description 3
- 230000011664 signaling Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229940035044 sorbitan monolaurate Drugs 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 102000003390 tumor necrosis factor Human genes 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 2
- TWSWSIQAPQLDBP-CGRWFSSPSA-N (7e,10e,13e,16e)-docosa-7,10,13,16-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC(O)=O TWSWSIQAPQLDBP-CGRWFSSPSA-N 0.000 description 2
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-N 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 2
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 206010063409 Acarodermatitis Diseases 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 208000026872 Addison Disease Diseases 0.000 description 2
- 235000019489 Almond oil Nutrition 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- 206010003694 Atrophy Diseases 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 206010008479 Chest Pain Diseases 0.000 description 2
- 201000006082 Chickenpox Diseases 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 102100026515 Cytochrome P450 2S1 Human genes 0.000 description 2
- 206010012426 Dermal cyst Diseases 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- 206010012455 Dermatitis exfoliative Diseases 0.000 description 2
- 206010012468 Dermatitis herpetiformis Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 208000010305 Epidermal Cyst Diseases 0.000 description 2
- 208000035874 Excoriation Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 208000003807 Graves Disease Diseases 0.000 description 2
- 208000015023 Graves' disease Diseases 0.000 description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 2
- 101000855328 Homo sapiens Cytochrome P450 2S1 Proteins 0.000 description 2
- 206010022562 Intermittent claudication Diseases 0.000 description 2
- 208000002260 Keloid Diseases 0.000 description 2
- 206010023330 Keloid scar Diseases 0.000 description 2
- 238000008214 LDL Cholesterol Methods 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 201000009053 Neurodermatitis Diseases 0.000 description 2
- 206010054107 Nodule Diseases 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 206010033733 Papule Diseases 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- 208000031845 Pernicious anaemia Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000000528 Pilonidal Sinus Diseases 0.000 description 2
- 206010035043 Pilonidal cyst Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 208000004550 Postoperative Pain Diseases 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 238000003559 RNA-seq method Methods 0.000 description 2
- 208000033464 Reiter syndrome Diseases 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- 241000447727 Scabies Species 0.000 description 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 2
- 206010039796 Seborrhoeic keratosis Diseases 0.000 description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 description 2
- 206010040954 Skin wrinkling Diseases 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010042971 T-cell lymphoma Diseases 0.000 description 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 2
- 208000024780 Urticaria Diseases 0.000 description 2
- 206010046980 Varicella Diseases 0.000 description 2
- 206010047642 Vitiligo Diseases 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 208000009621 actinic keratosis Diseases 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- TWSWSIQAPQLDBP-UHFFFAOYSA-N adrenic acid Natural products CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O TWSWSIQAPQLDBP-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 108060000307 allene oxide cyclase Proteins 0.000 description 2
- 239000008168 almond oil Substances 0.000 description 2
- 231100000360 alopecia Toxicity 0.000 description 2
- NPDSHTNEKLQQIJ-ZJHFMPGASA-N alpha-dimorphecolic acid Chemical compound CCCCC\C=C/C=C/C(O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-ZJHFMPGASA-N 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 238000002583 angiography Methods 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000037444 atrophy Effects 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- 239000003855 balanced salt solution Substances 0.000 description 2
- 210000004082 barrier epithelial cell Anatomy 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000031018 biological processes and functions Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 208000037976 chronic inflammation Diseases 0.000 description 2
- 230000006020 chronic inflammation Effects 0.000 description 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 2
- 238000001360 collision-induced dissociation Methods 0.000 description 2
- 229940125878 compound 36 Drugs 0.000 description 2
- 229940125844 compound 46 Drugs 0.000 description 2
- 229940126545 compound 53 Drugs 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NPDSHTNEKLQQIJ-UHFFFAOYSA-N dimorphecolic acid Natural products CCCCCC=CC=CC(O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000004890 epithelial barrier function Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002221 fluorine Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 230000001969 hypertrophic effect Effects 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000007913 intrathecal administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 210000001117 keloid Anatomy 0.000 description 2
- 238000011813 knockout mouse model Methods 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 206010025135 lupus erythematosus Diseases 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- RIZOOQYPYGPBOC-UHFFFAOYSA-N methyl 9-hydroxynonanoate Chemical compound COC(=O)CCCCCCCCO RIZOOQYPYGPBOC-UHFFFAOYSA-N 0.000 description 2
- SXKMLYGXKLNTRS-UHFFFAOYSA-N methyl decinoate Natural products COC(=O)CCCCCCCC#C SXKMLYGXKLNTRS-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 210000001616 monocyte Anatomy 0.000 description 2
- 210000002433 mononuclear leukocyte Anatomy 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 206010028417 myasthenia gravis Diseases 0.000 description 2
- 239000006199 nebulizer Substances 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 230000002981 neuropathic effect Effects 0.000 description 2
- 208000021722 neuropathic pain Diseases 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000004305 normal phase HPLC Methods 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000008389 polyethoxylated castor oil Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 238000004393 prognosis Methods 0.000 description 2
- 208000017940 prurigo nodularis Diseases 0.000 description 2
- 238000003127 radioimmunoassay Methods 0.000 description 2
- 208000002574 reactive arthritis Diseases 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 201000004700 rosacea Diseases 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 208000005687 scabies Diseases 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 description 2
- 201000003385 seborrheic keratosis Diseases 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 210000002972 tibial nerve Anatomy 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- VNYSSYRCGWBHLG-PHKHWAPOSA-N (5s,6z,8e,10e,12r,14z)-6,7,14,15-tetradeuterio-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid Chemical compound CCCCCC(/[2H])=C(/[2H])C[C@@H](O)\C=C\C=C\C(\[2H])=C(\[2H])[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-PHKHWAPOSA-N 0.000 description 1
- UQQPKQIHIFHHKO-XVTLYKPTSA-N (5z,8z)-octadeca-5,8-dienoic acid Chemical class CCCCCCCCC\C=C/C\C=C/CCCC(O)=O UQQPKQIHIFHHKO-XVTLYKPTSA-N 0.000 description 1
- KFINXCASWPGHEW-UHFFFAOYSA-N (9S*,10R*,11R*,12Z,15Z)-9,10,11-trihydroxyoctadeca-12,15-dienoic acid Natural products CCC=CCC=CC(O)C(O)C(O)CCCCCCCC(O)=O KFINXCASWPGHEW-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- LVBXEMGDVWVTGY-VOTSOKGWSA-N (E)-oct-2-enal Chemical compound CCCCC\C=C\C=O LVBXEMGDVWVTGY-VOTSOKGWSA-N 0.000 description 1
- KAANTNXREIRLCT-UHFFFAOYSA-N 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)C)C1=CC=CC=C1 KAANTNXREIRLCT-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- SUKFODPXCOKBIA-UHFFFAOYSA-N 11-hydroxy-11-(3-pentyloxiran-2-yl)undec-2-enoic acid Chemical compound O1C(C(CCCCCCCC=CC(=O)O)O)C1CCCCC SUKFODPXCOKBIA-UHFFFAOYSA-N 0.000 description 1
- HNICUWMFWZBIFP-IRQZEAMPSA-N 13(S)-HODE Chemical compound CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O HNICUWMFWZBIFP-IRQZEAMPSA-N 0.000 description 1
- HNICUWMFWZBIFP-BSZOFBHHSA-N 13-HODE Chemical compound CCCCCC(O)\C=C\C=C/CCCCCCCC(O)=O HNICUWMFWZBIFP-BSZOFBHHSA-N 0.000 description 1
- ZFULIMDGARVKBJ-UHFFFAOYSA-N 18,18,18-trihydroxyoctadec-2-enoic acid Chemical compound OC(CCCCCCCCCCCCCCC=CC(=O)O)(O)O ZFULIMDGARVKBJ-UHFFFAOYSA-N 0.000 description 1
- VHLMOQIWCILIDK-UHFFFAOYSA-N 2,2-dimethylpropanoic acid methyl 2-methylpropanoate Chemical compound COC(=O)C(C)C.CC(C)(C)C(O)=O VHLMOQIWCILIDK-UHFFFAOYSA-N 0.000 description 1
- NXVZDSCEUVMQOC-UHFFFAOYSA-N 2,3-dihydroxyoctadec-2-enoic acid Chemical class CCCCCCCCCCCCCCCC(O)=C(O)C(O)=O NXVZDSCEUVMQOC-UHFFFAOYSA-N 0.000 description 1
- NXRGKFVQYZGDIY-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1.CC1=CC=CC(C)=N1 NXRGKFVQYZGDIY-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- CWJSCIWGSUCULS-UHFFFAOYSA-N 2-hydroperoxyicosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCC=CC=CC=CC=C(OO)C(O)=O CWJSCIWGSUCULS-UHFFFAOYSA-N 0.000 description 1
- NOCWDMQAHCQAKS-UHFFFAOYSA-N 2-hydroxyoctadeca-2,4-dienoic acid Chemical class CCCCCCCCCCCCCC=CC=C(O)C(O)=O NOCWDMQAHCQAKS-UHFFFAOYSA-N 0.000 description 1
- RVEJRPJGKXTQIF-UHFFFAOYSA-M 2-oxoethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=O)C1=CC=CC=C1 RVEJRPJGKXTQIF-UHFFFAOYSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BNNMDMGPZUOOOE-UHFFFAOYSA-N 4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 BNNMDMGPZUOOOE-UHFFFAOYSA-N 0.000 description 1
- GNYDYUQVALBGGZ-UHFFFAOYSA-N 7-bromohept-1-ene Chemical compound BrCCCCCC=C GNYDYUQVALBGGZ-UHFFFAOYSA-N 0.000 description 1
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
- NTVFQBIHLSPEGQ-SYMVGPSASA-N 9,10,13-trihome Chemical compound CCCCC[C@H](O)\C=C\[C@@H](O)[C@@H](O)CCCCCCCC(O)=O NTVFQBIHLSPEGQ-SYMVGPSASA-N 0.000 description 1
- AWGKNMHZKQBIRD-UHFFFAOYSA-N 9,10,13-trihydroxy-2,2-dimethyloctadec-3-enoic acid Chemical compound CCCCCC(CCC(C(CCCCC=CC(C)(C)C(=O)O)O)O)O AWGKNMHZKQBIRD-UHFFFAOYSA-N 0.000 description 1
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
- ZBLJVJUPSJWHMY-UHFFFAOYSA-N 9-hydroxy-2,2,3-trimethylnonanoic acid Chemical compound CC(C(=O)O)(C(CCCCCCO)C)C ZBLJVJUPSJWHMY-UHFFFAOYSA-N 0.000 description 1
- 101150053849 ALOXE3 gene Proteins 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- MZQXAWAWDWCIKG-SPSBLGDNSA-N Avenoleic acid Chemical compound CCC[C@@H](O)C\C=C/C\C=C/CCCCCCCC(O)=O MZQXAWAWDWCIKG-SPSBLGDNSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 108010074051 C-Reactive Protein Proteins 0.000 description 1
- 102100032752 C-reactive protein Human genes 0.000 description 1
- HSZKTQLDHIHWBN-QGZVFWFLSA-N C1[C@H](O1)CCCCCCCCC=CCCCCCC(=O)O Chemical compound C1[C@H](O1)CCCCCCCCC=CCCCCCC(=O)O HSZKTQLDHIHWBN-QGZVFWFLSA-N 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108700021993 Cytochrome P-450 CYP2J2 Proteins 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- 102100039104 Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD1 Human genes 0.000 description 1
- 235000021297 Eicosadienoic acid Nutrition 0.000 description 1
- 206010049119 Emotional distress Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- LRIBLGDQCAXBOV-UJWAFZRWSA-N FC=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O.[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1 Chemical compound FC=1C(NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C1)=O)=O.[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1 LRIBLGDQCAXBOV-UJWAFZRWSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 102100026833 Group IIF secretory phospholipase A2 Human genes 0.000 description 1
- 206010062639 Herpes dermatitis Diseases 0.000 description 1
- 101000884921 Homo sapiens Dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit DAD1 Proteins 0.000 description 1
- 101000983156 Homo sapiens Group IIF secretory phospholipase A2 Proteins 0.000 description 1
- 101000620022 Homo sapiens Hydroperoxide isomerase ALOXE3 Proteins 0.000 description 1
- 101000983161 Homo sapiens Phospholipase A2, membrane associated Proteins 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000003820 Lipoxygenases Human genes 0.000 description 1
- 108090000128 Lipoxygenases Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 238000000585 Mann–Whitney U test Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- HSZKTQLDHIHWBN-KRWDZBQOSA-N OC(CCCCCC=CCCCCCCCC[C@@H]1OC1)=O Chemical compound OC(CCCCCC=CCCCCCCCC[C@@H]1OC1)=O HSZKTQLDHIHWBN-KRWDZBQOSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010034277 Pemphigoid Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 102100026831 Phospholipase A2, membrane associated Human genes 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 101710111205 Polyunsaturated fatty acid lipoxygenase ALOX15B Proteins 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 238000011530 RNeasy Mini Kit Methods 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000005867 T cell response Effects 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SWJBITNFDYHWBU-UHFFFAOYSA-N [I].[I] Chemical compound [I].[I] SWJBITNFDYHWBU-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 230000000307 algesic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940030999 antipsoriatics Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000006470 autoimmune attack Effects 0.000 description 1
- 230000037365 barrier function of the epidermis Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WWIWLTSSHDKOKO-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1 WWIWLTSSHDKOKO-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 238000009534 blood test Methods 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 208000000594 bullous pemphigoid Diseases 0.000 description 1
- OVYQSRKFHNKIBM-UHFFFAOYSA-N butanedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)CCC(O)=O OVYQSRKFHNKIBM-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical group [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 210000000511 carpometacarpal joint Anatomy 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000009535 clinical urine test Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 101150112582 dad2 gene Proteins 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 description 1
- 238000001378 electrochemiluminescence detection Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012645 endogenous antigen Substances 0.000 description 1
- 230000008497 endothelial barrier function Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 210000005175 epidermal keratinocyte Anatomy 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- URTXPBSKBBUFNK-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O.CCS(O)(=O)=O URTXPBSKBBUFNK-UHFFFAOYSA-N 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000011124 ex vivo culture Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical group 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 210000004884 grey matter Anatomy 0.000 description 1
- 235000021137 habitual diet Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- VWCDKQVEOINBJR-UHFFFAOYSA-N hex-2-enoic acid Chemical compound C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O.C(C=CCCC)(=O)O VWCDKQVEOINBJR-UHFFFAOYSA-N 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000005722 itchiness Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-M leukotriene B4(1-) Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC([O-])=O VNYSSYRCGWBHLG-AMOLWHMGSA-M 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- QBNOPZJAURRQCE-UHFFFAOYSA-M magnesium;prop-1-yne;bromide Chemical compound [Mg+2].[Br-].CC#[C-] QBNOPZJAURRQCE-UHFFFAOYSA-M 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- VORKGRIRMPBCCZ-UHFFFAOYSA-N methyl tricosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(=O)OC VORKGRIRMPBCCZ-UHFFFAOYSA-N 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003990 molecular pathway Effects 0.000 description 1
- 235000021084 monounsaturated fats Nutrition 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 238000002552 multiple reaction monitoring Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000944 nerve tissue Anatomy 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 229940124583 pain medication Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000010149 post-hoc-test Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000002540 product ion scan Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- SXBRULKJHUOQCD-UHFFFAOYSA-N propanoic acid Chemical compound CCC(O)=O.CCC(O)=O SXBRULKJHUOQCD-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001823 pruritic effect Effects 0.000 description 1
- 230000003025 pruritogenic effect Effects 0.000 description 1
- 230000001337 psychedelic effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000007388 punch biopsy Methods 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 210000002804 pyramidal tract Anatomy 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000027223 regulation of cytokine secretion Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000000697 sensory organ Anatomy 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000008591 skin barrier function Effects 0.000 description 1
- 238000007390 skin biopsy Methods 0.000 description 1
- 230000036620 skin dryness Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000010009 steroidogenesis Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000001839 systemic circulation Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/92—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving lipids, e.g. cholesterol, lipoproteins, or their receptors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Endocrinology (AREA)
- Biophysics (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762529846P | 2017-07-07 | 2017-07-07 | |
US62/529,846 | 2017-07-07 | ||
PCT/US2018/041086 WO2019010414A1 (en) | 2017-07-07 | 2018-07-06 | FATTY ACID DERIVATIVES AND USE THEREOF |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20200027545A true KR20200027545A (ko) | 2020-03-12 |
Family
ID=63036390
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020207003568A KR20200027545A (ko) | 2017-07-07 | 2018-07-06 | 지방산 유도체 및 이의 용도 |
Country Status (8)
Country | Link |
---|---|
US (2) | US11555021B2 (ja) |
EP (1) | EP3649115B1 (ja) |
JP (1) | JP7234151B2 (ja) |
KR (1) | KR20200027545A (ja) |
CN (1) | CN110869354A (ja) |
AU (1) | AU2018297192B2 (ja) |
CA (1) | CA3064132C (ja) |
WO (1) | WO2019010414A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US12018159B2 (en) | 2016-07-29 | 2024-06-25 | Sony Group Corporation | Ultra bright dimeric or polymeric dyes and methods for preparation of the same |
JP7551056B2 (ja) | 2017-10-05 | 2024-09-17 | ソニーグループ株式会社 | プログラマブルなポリマー薬物 |
KR20200108866A (ko) | 2018-01-12 | 2020-09-21 | 소니 주식회사 | 생물학적 활성 화합물을 포함하는 강성 공간 군을 갖는 중합체 |
EP3814366A1 (en) | 2018-06-27 | 2021-05-05 | Sony Corporation | Polymeric dyes with linker groups comprising deoxyribose |
CN113121475B (zh) * | 2021-03-30 | 2022-12-02 | 香港科技大学深圳研究院 | 不饱和脂肪酸类化合物及其制备方法和应用 |
CN113620923B (zh) * | 2021-07-16 | 2023-03-14 | 扬州工业职业技术学院 | 一种低温电解液添加剂的制备方法及应用 |
CN115073295B (zh) * | 2022-07-21 | 2023-12-26 | 山东大学 | 马齿苋中不饱和脂肪酸及其提取分离方法和应用 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5055613A (en) * | 1988-02-18 | 1991-10-08 | G. D. Searle & Co. | Metabolites of pentanedioic acid derivatives |
ATE168372T1 (de) * | 1993-03-29 | 1998-08-15 | Hsc Res Dev Lp | Hepoxilin analoga verwendbar als entzündungshemmende mittel |
US20020037876A1 (en) * | 1998-06-25 | 2002-03-28 | Yissum Research Development Company Of Hebrew University Of Jerusalem | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
US7304093B2 (en) | 2000-10-11 | 2007-12-04 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
SI2404890T1 (sl) | 2003-01-23 | 2017-12-29 | Esperion Therapeutics Inc. | Hidroksilne spojine in sestavki za uravnavanje holesterola in sorodne uporabe |
WO2006106438A2 (en) * | 2005-01-11 | 2006-10-12 | Evolva Sa | Modulators of ppar activity |
JP5337479B2 (ja) | 2005-05-04 | 2013-11-06 | プロノヴァ・バイオファーマ・ノルゲ・アーエス | 新規化合物 |
IL181577A0 (en) | 2007-02-26 | 2007-07-04 | Jacob Bar Tana | Combination therapy composition and methods for the treatment of cardiovascular disorders and immune-related disorders |
WO2010027762A1 (en) | 2008-09-04 | 2010-03-11 | Boehringer Ingelheim International Gmbh | Indolizine inhibitors of leukotriene production |
WO2013157926A1 (en) | 2012-04-19 | 2013-10-24 | Nyken Holding B.V. | Geranyl geranyl acetone analogs and uses thereof |
JP6160375B2 (ja) | 2013-09-06 | 2017-07-12 | ブラザー工業株式会社 | 画像記録装置 |
-
2018
- 2018-07-06 KR KR1020207003568A patent/KR20200027545A/ko active IP Right Grant
- 2018-07-06 CA CA3064132A patent/CA3064132C/en active Active
- 2018-07-06 JP JP2019572570A patent/JP7234151B2/ja active Active
- 2018-07-06 US US16/622,697 patent/US11555021B2/en active Active
- 2018-07-06 EP EP18746415.1A patent/EP3649115B1/en active Active
- 2018-07-06 WO PCT/US2018/041086 patent/WO2019010414A1/en unknown
- 2018-07-06 CN CN201880045287.6A patent/CN110869354A/zh active Pending
- 2018-07-06 AU AU2018297192A patent/AU2018297192B2/en active Active
-
2022
- 2022-04-12 US US17/718,965 patent/US20220274940A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
US20220274940A1 (en) | 2022-09-01 |
JP2020526505A (ja) | 2020-08-31 |
CA3064132A1 (en) | 2019-01-10 |
WO2019010414A1 (en) | 2019-01-10 |
EP3649115A1 (en) | 2020-05-13 |
CN110869354A (zh) | 2020-03-06 |
EP3649115B1 (en) | 2024-09-04 |
AU2018297192A1 (en) | 2019-12-19 |
US20210139440A1 (en) | 2021-05-13 |
US11555021B2 (en) | 2023-01-17 |
CA3064132C (en) | 2024-06-04 |
AU2018297192B2 (en) | 2022-02-17 |
JP7234151B2 (ja) | 2023-03-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR20200027545A (ko) | 지방산 유도체 및 이의 용도 | |
Levy | Resolvins and protectins: natural pharmacophores for resolution biology | |
Colas et al. | Identification and signature profiles for pro-resolving and inflammatory lipid mediators in human tissue | |
Serhan et al. | E-series resolvin metabolome, biosynthesis and critical role of stereochemistry of specialized pro-resolving mediators (SPMs) in inflammation-resolution: Preparing SPMs for long COVID-19, human clinical trials, and targeted precision nutrition | |
US6416965B2 (en) | Screening methods for presqualene disphosphate analogs | |
Serhan | Mediator lipidomics | |
Tungen et al. | Synthesis and anti-inflammatory and pro-resolving activities of 22-OH-PD1, a monohydroxylated metabolite of protectin D1 | |
Batsika et al. | Saturated oxo fatty acids (SOFAs): A previously unrecognized class of endogenous bioactive lipids exhibiting a cell growth inhibitory activity | |
CA3083907A1 (en) | Alleviating oxidative stress disorders with pufa derivatives | |
EP3287437B1 (en) | Enantiomers of 2-hydroxide derivatives of fatty acids | |
JP6820312B2 (ja) | アトルバスタチンにより増加し、炎症を消失させる新規な13−シリーズのレゾルビンの解明 | |
WO2008063768A2 (en) | Compositions and methods for treating metabolic diseases | |
JP2021525803A (ja) | カンナビノイド及びそれらの使用 | |
KR20180066395A (ko) | 유리 지방산을 포함하는 특발성 폐섬유증 예후예측용 바이오마커 | |
JPH09268153A (ja) | トリフルオロメチルケトン誘導体及びホスホリパーゼa2阻害剤 | |
Li et al. | Pulmonary delivery of specialized pro-resolving mediators-based nanotherapeutics attenuates pulmonary fibrosis in preclinical animal models | |
EP3746066A1 (en) | Disease detection and treatment based on trimethyl-lysine levels | |
JP2023523051A (ja) | 脂質代謝関連疾患の予防又は治療用化合物 | |
US20050234025A1 (en) | Compositions comprising one or more policosanols and/or policosanoic acids combined with sterol and/or steroid based ascorbic acid derivatives, and uses thereof | |
EP1231913A2 (en) | Treatment of cyclooxygenase-2 mediated disorders using conjugated fatty acid compounds | |
JP4836345B2 (ja) | 環状ホスファチジン酸誘導体を含む神経細胞の生存促進剤 | |
Patel et al. | 5-Oxo-15-HETE: Total synthesis and bioactivity | |
CN108473518A (zh) | 新双膦酸化合物 | |
Okuno et al. | Metabolism and biological functions of 12 (S)-hydroxyheptadeca-5Z, 8E, 10E-trienoic acid | |
Kovtun et al. | Retinoids in dermatology: functional activity and prospects of synthetic analogues |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right |